1,1'-Carbonyl-di-(1,2,4-triazole) → HCID 131734789, compound

Participants

Reaction Steps

A solution of di(1H-1,2,4-triazol-1-yl)methanone (2.78 g, 15.23 mmol) in DMF (15 ml) was added to 6-amino-4-((2-methoxyethyl)amino)nicotinonitrile (intermediate 75, 2.96 g, 15.23 mmol) in anhydrous DMF (15 ml) at 0° C. After stirring for 2.5 h at room temperature a solution of 2-(trimethylsilyl)ethyl 4-((2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-3-oxopiperazine-1-carboxylate (intermediate 123, 2.83 g, 6.09 mmol) in DMF (20 ml) was added. The reaction mixture was stirred for 17.5 h at room temperature, then partitioned between saturated aqueous NaHCO3 solution and EtOAc, the EtOAc phase washed with brine, dried over MgSO4 and evaporated. The residue was applied to a RediSep® silica column and purified by normal phase chromatography, eluting with EtOAc then a gradient from hexane to 50% EtOAc in hexane. Product containing fractions were combined and evaporated to give the title compound as a clear pale yellow oil. (UPLC-MS 7) tR 1.28; ESI-MS 683.5 [M+H]+.

Provenance & Evidence